


Five Times Stiles Doesn’t Actually Need A Condom (And One Time He Does)

by otter



Category: Teen Wolf (TV)
Genre: Blow Jobs, Condoms, M/M, Safer Sex, Sex Education
Language: English
Status: Completed
Published: 2013-02-26
Updated: 2013-02-26
Packaged: 2017-12-03 16:35:40
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 14,481
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/700399
Author URL: https://archiveofourown.org/users/otter/pseuds/otter
Summary: <blockquote class="userstuff">
              <p>Stiles doesn't actually mean to become Beacon Hills High's go-to guy for free condoms and sex advice. It just happens.</p>
            </blockquote>





	Five Times Stiles Doesn’t Actually Need A Condom (And One Time He Does)

**Author's Note:**

  * For [abbylee](https://archiveofourown.org/users/abbylee/gifts).
  * Translation into 中文 available: [[翻譯]Five Times Stiles Doesn’t Actually Need A Condom (And One Time He Does) 5次Stiles用不著安全套 (1次他終於用得著) by otter](https://archiveofourown.org/works/3799654) by [malucko](https://archiveofourown.org/users/malucko/pseuds/malucko)



> This is a story that is romantically devoted to safer sex. I've done my utmost to make it both entertaining and educational, but if you feel I've gotten anything terribly wrong please feel free to tell me the comments or in my askbox on [my tumblr](http://agentotter.tumblr.com).
> 
> This story also turned me into a neurotic mess of a former human being, and I must give my undying devotion to DevilDoll, abbylee, hatteress, and verity for all bearing with me through my time of manic insanity. I'm kind of always like that but this was _especially_ bad, let me tell you. Also, it's entirely abbylee's fault. ENTIRELY.

1.

By the time he hits high school, Stiles feels like he’s got a pretty good handle on the whole sex thing. He hasn’t really had a formal sex education — the single day they spent on it in sixth grade was heavy on hormonal changes and light on specifics, and as yet nobody’s offered him any hands-on time — but Stiles has his sources. He’s got the Internet, for a start, of which he is the _master_ , and it’s certainly a font of knowledge (dirty, dirty knowledge), but he’s sure that a lot of what he finds there is either theoretical or porn-based.

He’s watched enough porn, of course, to know that it’s not really a good source of information on common sexual practices, not to mention the average level of flexibility in the female body. It’s also not very good for his self-esteem, once he starts branching out into the guy-on-guy stuff, because he is seriously _never_ going to have those abs. It’s useful at least for helping him figure out his preferences. He discovers the rich and verdant world of his own kinks. He gets in a lot of practice with touching his own dick, anyway, and learns that quite a few positions he believed to be nothing more than Internet myth are actually possible. With a contortionist.

He’s got some primary sources, too, because it pays to be thorough. He takes lunch in for his dad one afternoon and ends up spending an hour afterward chatting with a prostitute named Cindy Lou. (He’s sure it’s not her real name and that she’s waiting for Deputy Saunders to figure out it’s actually a knock-knock joke.) She seems to appreciate his professional interest, and their time together is _very_ educational, right up until Stiles’ dad comes out of his office and drags Stiles away by the arm, practically throwing him out the station’s front door.

His dad’s actually not bad either, as far as frank discussion goes. There are some things Stiles is _never_ going to ask, in some cases because he fears the answers and others because he refuses to incriminate himself. But Stiles’ dad is pretty inured by now to the random questions that pop out of his son’s mouth. When they start straying away from subjects like hypothetical zombie apocalypse scenarios and into hypothetical sex scenarios, Dad just takes it in his stride. He seems kind of relieved to not have to have any sort of formal sex talk, and he always answers Stiles’ questions to the best of his ability. The fact that he manages to do it with a mostly straight face is frankly impressive. He even sits through a twenty-minute discourse on the history of syphilis, with a side-ramble on Columbian theory versus pre-Columbian theory, and even if he’s not actually listening anymore after the first five minutes, it’s still the thought that counts.

The point is, with all of these excellent resources at his disposal, not to mention his own formidable research skills, he’s pretty sure he’s got this. He knows that one day he’s going to convince somebody to sleep with him — he’s still holding out hope that Lydia will eventually recognize that their genius babies could rule the world — and he’s pretty sure it’s going to be awesome, at least in part because he knows his stuff.

And then he has health class sophomore year with Coach Finstock, and all of his illusions are shattered.

Finstock opens on the first day with, “There are three rules that I live by: Never get less than twelve hours sleep. Never play cards with a guy who has the same first name as a city. And never get involved with a woman who has a tattoo of a dagger on her body. Now you stick to that, and everything else is cream cheese.”

It’s probably accurate, at least, if by “cream cheese” Coach means “a sticky mess that starts to reek horribly if you leave it to its own devices.” Finstock’s version of “health class” makes _no sense._

Coach doesn’t really teach the stuff that’s in the textbook, like eating nutritious foods or getting plenty of exercise. He’s a coach, so he probably _knows_ all that, but he ends up giving hour-long diatribes about healing crystals and acupuncture and the time he signed up for a tai chi class that ended up being held at an all-nude resort for senior citizens. When they finally get to the sex-education portion of the class, it ends up being a little… advanced. Sure, Stiles walks away from it knowing an awful lot about the fundamentals of tantric sex, negotiating bondage scenes, and the opportunities that role-play can provide in spicing up a marriage, but he feels like the whole thing’s been a little thin on the essentials.

He doesn’t realize it’s a full-on emergency situation until Finstock breaks out the bananas.

“I didn’t know anybody actually _did_ this in class,” Stiles says. He’s got a wrapped condom in one hand and a really overripe banana in the other. “I thought this was totally a sitcom scenario.”

Scott’s not even listening. His mouth’s hanging open and he’s watching a girl in the next row who’s showing off for an incredibly appreciative crowd by demonstrating her ability to apply a condom to a banana with just her mouth.

Finstock’s watching, too, and it’s really creepy in a bad-wrong kind of way until the girl finishes and he snaps, “No! Wrong! You’ve left air in the reservoir tip and when your banana comes you’re going to have a burst condom and banana milkshake all over the place.” He snatches the banana and condom that Greenberg’s holding right out of the kid’s hands, says, “Here, allow me to demonstrate,” and then proceeds to do just that.

Well, Stiles assumes he does. Stiles turns away before he can be scarred for life, and he even reaches out and physically turns Scott’s head, too, because he’s a good friend like that.

“Condoms are more complicated than I thought,” Scott says. He’s blinking down at his banana with a dazed expression, like he’s trying to figure out his angle of approach and how to keep his teeth out of the way.

“Nah, man, it’s simple,” Stiles says. He plucks Scott’s condom out of his hands and tears the packaging carefully open with his fingers. “Step one: Treat the condom like a delicate flower. Don’t do anything that could break it, like opening the foil with your teeth or poking a sharp fingernail into the middle of it or giving it to your pet hedgehog as a toy. Step two: Pinch the tip. We’ve already learned a valuable and psychologically damaging lesson on this subject courtesy of Coach. Step three: Roll that bad boy down your… uh… banana. And you’re done!”

The banana looks a little bit silly with a condom on it, but that’s nothing compared to how Scott looks, brandishing his latex-coated banana like he’s proud of his creation. Jackson must think so, too, because when Stiles leans back to survey his good works, he sees Jackson in the next row over, watching them with a vicious grin on his face as he records the whole thing on his phone.

“Nice, Stilinski,” he says. “You looked like you enjoyed getting your hands on McCall’s fruit salad. You should try going down on it, you could have a great career selling fifty-cent blowjobs.”

“And you’re apparently going to have a fantastic life as a skeevy amateur porn cameraman,” Stiles says. He’s fucking proud of his condom skills; he doesn’t give a shit if Jackson puts that video up on YouTube, Stiles _owned_ that banana.

It doesn’t matter, though, because that’s when Finstock swoops in like the avenging hand of the sex ed gods, snatching the phone out of Jackson’s hands and shouting, “What part of _safe space_ are you not getting, Whittemore? _Red light!_ ” He shoves the phone into his own pocket in a way that implies that Jackson’s probably not going to get it back, ever.

Stiles smiles at Jackson and feels like vindication is his at last, at least until he picks up his own banana again. It’s so overripe that it droops limply in his grip, and it starts tearing in two before he even manages to get the condom rolled on to the tip of it.

“Aw, performance issues, Stilinski?” Jackson says, all mock-sympathy. Mock-everything really, because Stiles is pretty sure the guy doesn’t even _have_ feelings. “I hear it’s pretty common. Don’t worry, it’s no big deal, nobody’s ever gonna want to touch your dick anyway.”

Stiles _seriously_ considers making a _your mom seems to like it fine_ sort of joke, but Jackson’s touchy about that kind of thing, and Stiles gets it, so instead he lets it go. He turns to Scott, who’s still contemplating the banana like he doesn’t quite understand the mechanics of an item that’s really not any more complicated than a glove. For the penis.

“So if you put on two,” Greenberg says, “that’s better, right?”

Finstock’s leaning in over a terrified-looking girl and showing her how a condom can stretch down around his entire fist — Stiles does _not_ want to know — but he apparently hears the question and turns long enough to bark out, “If there’s more than one dick at the party, Greenberg, everybody puts on a raincoat!” before he goes back to terrorizing someone else.

“So, you _should_ put on two at once?” Scott hisses, keeping his voice down so Finstock doesn’t overhear and offer him anymore “helpful” advice. “Isn’t that bad? I thought I knew this stuff and I am so freaking confused right now. I’m going to get an F _and_ herpes.”

“Hey, come on, man, it’s not that bad,” Stiles says. He claps a consoling hand on Scott’s shoulder because the guy seriously looks like he’s got a headache coming on. “Except, okay, it _is_ that bad. It’s not you, it’s Coach. We’ll just put in some extra independent study time. That’s not a euphemism, by the way, I mean actual studying. On the Internet.”

Which is how they end up back at Stiles’ house after school, hunched together over Stiles’ laptop, while Stiles answers every question Scott can think of, and looks up the ones he’s never even thought to ask himself. It’s kind of a frightening glimpse into the dark recesses of Scott’s mind, but they’re bros, and that’s what bro-hood is for. When they’re both satisfied that Coach hasn’t completely ruined Scott’s chances of a normal sex life for good, they adjourn to the kitchen, where Stiles pulls a bunch of bananas out of the hanging fruit basket thing by the window.

“Oh man, not the bananas again,” Scott whines. “I can do it, Stiles, I swear.”

“So show me, dude,” Stiles says, handing the bananas off and digging into his pocket. He’s got a handful of condoms in there that he stole from Finstock’s desk earlier. They’re on the verge of expiring, which is probably the only reason Finstock sacrificed them to the cause of education, but he’s not exactly worried about the condoms breaking in this particular set of circumstances. “Just a little practice until you’re rolling them on like a champion.”

Scott sighs like Stiles is ruining his life, but he sits down at the dining room table and slips condoms on to banana after banana. There are four of them lying there on the counter when he’s done, neatly covered in slightly lubed latex. Scott’s hands have become increasingly adept and Stiles expresses his pride by putting his hands on Scott’s shoulders, giving them a supportive shake, and saying, “You’ve mastered the art, padawan. Congrats, you’ll totally be able to avoid syphilis now.”

Scott snorts, retreating into the kitchen to wash his hands and pick up his backpack. “Dude, that’s the one you get when you don’t eat oranges,” he says. Sometimes Stiles _swears_ that Scott says that sort of stuff just to mess with him, but most of the time he’s dead certain that it’s one hundred percent serious. He’s not sure which is worse.

“Yeah, great,” Stiles says. “We’ll just… revisit that topic at a later date. ‘Night, dude.”

Scott waves a hand on his way out, and Stiles settles in to Scott’s former seat at the dining room table. There are a bunch of sex-ready bananas with no party to go to, and he’s not sure he can actually eat them now either, even though the actual edible part hasn’t come into contact with any lubricated prophylactics. There’s also one condom left.

So of course, it’s when he’s trying to stretch it over his entire fist that his dad walks in. It’s kind of a testament to the strength of their relationship that he doesn’t just walk back out again.

“Science experiment?” his dad says hopefully.

“Nah,” Stiles answers. He doesn’t elaborate. It’s probably for the best.

2.

Stiles can only handle so many terrifying surprises in a single day.

Usually it’s his dad’s heart he’s worried about, but he’s starting to realize that his new life isn’t really conducive to good cardiac health, either. By the time he makes it back to the row of chairs outside Lydia’s hospital room — the ones he thinks of as being exclusively his — his heart rate’s almost returned to something like normal, but his adrenaline’s still through the roof. He closes his eyes, takes a few deep breaths, and reminds himself that he’s alive, even if he’s still not quite sure why, since he’s just had the kind of werewolf encounter that makes him question his own suicidal impulses.

He’s not sure what possessed him, this time, to be the one to shove _Derek_ against the wall and issue a series of increasingly improbable threats to Derek’s person, but he’s still kind of amazed that he didn’t end up gutted. Literally.

So when he opens his eyes at the same instant that Melissa McCall drops herself unceremoniously into the seat right next to him, he doesn’t react well. Actually, he yelps out loud and flails so hard that he overbalances and tips his chair right over, sending himself sprawling into the middle of the corridor with a clattering, bone-jarring impact. He nearly trips Nurse Nancy, who already hates him to the point where, on a good day, she constantly looks like she’s five seconds away from shivving him with a pen.

“Oh my _god._ ” Stiles’ moan is half pain and half mortification.

Ms. McCall just raises an eyebrow at him, still sitting in her perfectly-upright chair, hands folded over her stomach. She’s not even holding in laughter; Stiles suspects that after years of the Stiles Stilinski Unintentional Slapstick routine, she’s probably just over it.

“So,” she says. It’s the word that’s launched a thousand uncomfortable conversations; Stiles expects this one won’t be any different, though it starts off just plain confusing when Ms. McCall continues with, “Who’s your friend?”

“My what now?” Stiles pulls himself to his feet, righting the furniture and cataloging his new aches and pains. He’s actually come off worse from hitting the floor than he did from getting all up in the face of a pissed-off Alpha werewolf so all things considered, he’s kind of a bad-ass today. He thinks he should probably be proud of himself but mostly he’s just regretting carrying his phone in his back pocket; he’s going to have phone-shaped bruises on his ass.

“The guy in the hall?” Ms. McCall prompts.

Stiles curses in his head, fluently and voluminously. He kind of _hates_ Derek right now, because everything is seriously Derek’s fault; the guy is a plague on Stiles’ house. It’s like Derek can somehow manage to screw up Stiles’ day just by getting up in the morning.

“You looked kind of, uh… _intimate._ ”

It takes a second for Ms. McCall’s next remark to really penetrate into Stiles’ brain, and then he has to look at her just to make sure that he’s really reading her tone correctly. He totally is. She’s giving him the kind of cautious, guarded look that says she’s trying to be the cool mom, the one kids can confide in, and also that her self-esteem is going to be totally crushed if he clams up now. It’s hesitant, searching, slightly pathetic, and it works on him _every time._ Which is why she uses it. Because Scott’s mom is like a thousand times craftier than anybody ever gives her credit for.

Since physically running away isn’t an option, Stiles just says, “Intimate?” like this is a spelling bee and he really wants to ask her to define the word.

“Yeah, you know,” Ms. McCall says. She waves a hand that kind of sweeps up and down her body, and Stiles isn’t sure what that’s supposed to mean. “You were kind of all over the guy, Stiles. And don’t try to tell me I didn’t see what I saw; I was only at the other end of the hallway and I’m not _blind_. I’m pretty sure the term _compromising position_ was invented for moments like that one.”

Stiles tries to imagine how it would have looked to see him and Derek from the far end of the hallway, the one that leads back to this ward. Ms. McCall didn’t get a good look at Derek, that much is obvious, or she’d probably be furious instead of teasing. Stiles’ body probably blocked most of Derek’s from her view. She wouldn’t have been able to see the way Derek’s eyes flashed red, but she would have seen the way Stiles shoved Derek back against the wall next to the stairwell, how Stiles’ hands twisted into Derek’s shirt, how Stiles pushed in close, his face undoubtedly red and livid, to tell Derek in no uncertain terms that no werewolf would ever again be touching a single precious hair on Lydia’s strawberry-blonde head, and—

And they must have _totally_ looked like they were passionately kissing. In the hospital corridor. _Fuck his life._

“Oh,” Stiles says. His mouth probably hangs open for entirely too long.

Stiles isn’t actually sure whether this is the worst misunderstanding that’s _ever_ happened to him or whether he’s incredibly flattered that there’s anybody in the world who thinks that Stiles could actually date somebody as hot as Derek Hale. Mostly, he’s relieved that he’s not going to have to come up with another lie to cover up exactly how werewolf-infested his whole life has become. It’s sort of nice to have somebody else assume the lie for him, especially since right now his brain is completely blank. He can’t think of a single thing to say to get out of this situation. He can’t think of a better cover story, either.

“Does he go to school with you?” Ms. McCall finally prompts, gently, like she thinks he’s about a foot away from falling into the proverbial deep end.

“School, yes,” Stiles agrees, numbly. “He’s um. A senior.”

Derek kind of _is_ from school, technically. He probably went to Beacon Hills High, years ago. He still lurks around there sometimes, like a total weirdo pervert. Plus, Stiles feels like once a guy’s been almost-fatally eviscerated on school grounds, that should give him a certain claim to the place.

“A senior, huh? I didn’t realize you were seeing anybody. Scott hasn’t said anything, and you know how he usually is about keeping secrets.”

Stiles’ laugh is kind of weak because yeah, he knows how Scott is about keeping secrets: formerly terrible, getting frighteningly good with intensive practice.

“Yeah, he’s not— he doesn’t know. About this.” And when he does, he’s going to laugh his head off, probably. Scott is the worst friend ever.

“Oh,” Ms. McCall says, and there’s a soft, wounded note in her voice that makes Stiles look up from where he’s been intensely examining his shoes. She puts a hand on his forearm and leans in closer. “Stiles, you know we— I mean, you have to realize that this doesn’t change _anything._ Me, Scott, probably everybody else, everybody who _matters_ … we’re still going to love you. No one’s going to care.”

Stiles says, “Yeah, I know.” He has to swallow around the lump in his throat because he _does_ know, and he’s not quite ready to even tackle this issue yet because he’s known for kind of a really long time that he’s not entirely heterosexual. It’s never seemed like a big thing, not when all of his focus has been on Lydia, anyway. He’s not prepared to put a name on it and make it a piece of him, when he’s still not even sure what _it_ is.

“Does your dad know?” Ms. McCall asks.

“ _No,_ ” Stiles replies, maybe a little too stridently, because when he comes out to his dad, _if_ he comes out, whatever _coming out_ is even going to mean for him, it is sure as shit _not_ going to be because of a relationship that he’s not even having.

Ms. McCall makes a wordless soothing noise and loops her arm all the way around his shoulders, pulling him in whether he likes it or not. He does like it, though, even if he feels a little guilty for putting her through this bizarre half-fake sexual identity crisis. He knows she never signed up for parenting _two_ teenage boys, but she’s still really good at it, and Stiles knows himself well enough to know that he is _not_ easy to parent. At all. Ever.

“I’m just not ready,” Stiles offers, because it’s the best excuse he can think of, and it also happens to be true.

“You don’t have to be,” Ms. McCall says. She presses a kiss to his hairline and then draws back, pinning him with an intense, do-not-bullshit-me-right-now look that he’s all too familiar with. “Are you being safe?”

“Safe?” Stiles repeats, quizzically, until it clicks in his brain exactly what she’s saying. “Oh! We’re not— it’s not— he’s not—”

“I’m not accusing you of anything, I just want to make sure you’re using protection, if and when you’re being intimate.”

“What, like because I’m kind of gay that means I’m slutty too?” Stiles says. He’s indignant and he kind of squawks a little but what the hell, seriously.

“ _No,_ ” Ms. McCall says, and even with that one word it’s clear she thinks he’s being kind of an idiot. He already regrets his word choice; he’s pretty sure she’s going to corner him later and they’re going to discuss that ‘slutty’ remark in greater detail. Stiles has made a terrible mistake. “I mean that physically the risk of transmission for some infections is higher with anal intercourse—” she ignores the way Stiles chokes on _air_ “—and there are additional bacterial infection risks. Not to mention that social stigmas can make it more difficult for people, _especially_ teenagers, in same-sex relationships to access appropriate health care. Safer sex isn’t about whether you’re monogamous or whether you trust the other person, it’s just about _safer sex._ Do you have condoms?”

“I… no?” Stiles says, weakly. He’s feeling kind of winded. He might actually be having a heart attack because Ms. McCall has just hit him with the hammer of uncomfortable anal sex talks. He doesn’t know how to deal with this, at all. Derek has _so much_ to answer for.

Ms. McCall gives him one last intense shoulder-squeeze, then gets up and vanishes into the room where they keep all the extra bandages, needles, and other things Stiles doesn’t want anywhere near his person. When she comes back, she’s got a brown paper bag that’s heavy with something; she presses it into his hands in such a way that he can’t possibly come up with a reason _not_ to take it. When he looks inside, it’s mostly condoms — a _lot_ of condoms — and some other things he doesn’t even _recognize_ just from looking at the packaging. There are a couple of brochures stuffed in on one side. Judging from the amount of supplies in there — supplies that will eventually expire and be no good to anyone — Stiles can only assume that Ms. McCall thinks he has an amazing, dazzling, incredibly active sex life.

With Derek Hale.

Jesus Christ.

“If you have any questions, you can ask me,” she says. “I’m not going to judge you, okay? There are a couple hotline numbers in there, too, if that’s better for you.”

“Thanks, Ms. McCall,” Stiles mumbles. “I’ve got to. Um. I should go. Home.” He can’t look at her. He reaches for his backpack instead, picks it up from underneath the row of chairs where he haphazardly flung it when he first arrived. He rolls up the bag full of packaged latex products and shoves it all the way into the bottom of the outside pocket, which he uses for basically nothing. This way there’s no chance at all that he might reach in to get something else and instead end up spilling condoms all over the floor.

Stiles knows his life, and that’s exactly what could happen, if he’s not careful.

“Just let me know if you need more,” Ms. McCall says, and Stiles would like to know when she became such an optimist.

“Thanks!” Stiles replies, forced-chipper, and even throws in an awkward wave as he backs down the hall, trying to make good his escape. “I definitely won’t, thank you, bye!”

He makes it to the bank of elevators and frantically pushes the down button, but life doesn’t work like the movies. Stiles knows this from personal experience. The elevator is never just there waiting when you need it; it’s impossible to just unleash one last witty quip and then make a dramatic exit. That stuff only works for werewolves; if Derek is anything to go by, Stiles can only assume that flair is part of their genetic heritage.

But thankfully, mercifully, life is not like the movies in other ways, too. Ms. McCall is at work, and she doesn’t have any more time to badger him about his non-existent personal life. She goes back behind the nurse’s station — where she receives a high-five from Nurse Nancy, who is apparently delighted to know that she can now use awkward sex talks to get Stiles to flee the entire floor — and then the elevator comes, _finally,_ and Stiles scrambles inside like it’s his own personal panic room.

3.

It’s not so much that Stiles _forgets_ about the safer sex arsenal that he’s carrying around in his backpack. It’s more like he’s attempting to repress basically all of the events surrounding said items. So he’s not thinking about sex at all right now. (He’s certainly not thinking about sex with Derek, he definitely hasn’t been beating off to that idea every night for the last week.) He’s standing at his locker after lacrosse practice, still dripping from the shower, and he isn’t really thinking about anything in particular, except whether it’s ethically wrong to eat an entire pizza by himself when he could, theoretically, invite his best friend.

Then he hears Greenberg say, “She says she wants to save her virginity, you know, for when she’s married. But she says anal doesn’t count, so we’re totally going to do that. Plus I don’t even have to use a condom! It’s not like she can get pregnant or something.”

Stiles stops. He just stops everything. There are two reasons that he seriously _cannot_ believe what he’s hearing. The first reason is that he’s never imagined anybody wanting to have sex with Greenberg and he’s trying really hard not to imagine it now, even with all evidence pointing to the fact that Greenberg is going to have sex. Even if he doesn’t seem to think it’s sex. The second reason is that he’s heard Greenberg say a _lot_ of stupid things, but he’s never actually heard Greenberg say anything _quite_ this stupid.

Stiles turns to look, like maybe he can discern some sort of visible sign of how anybody can be that moronic and live. Greenberg’s just standing in front of his locker, though, looking the same as he always does. Velazquez, at the locker next to his, is standing there nodding, like Greenberg’s speaking truth to power or something.

Danny, whose locker is down the row from Greenberg’s, is standing there half naked, frozen in the act of buttoning up his jeans like he’s completely unable to deal with the reality of this situation. Stiles catches Danny’s eye, and sees his own horror reflected there.

“Uh, Greenberg,” Danny says, because he’s a nice guy, he’s not going to let his teammate make this big a mistake, even if there probably isn’t a way to actually make him smarter. Because _Greenberg._ “You do realize that’s still sex, right? It doesn’t stop counting just because you’re using a different hole, man.”

“Well, she’s done it before and she’s still a virgin,” Greenberg says. “Anyway, how would you know? You’re gay, Danny, you’ve never had sex with a girl, come on.” He smirks like he thinks he’s just outwitted somebody for the first time ever.

The sound Stiles makes is somewhere between an incredulous laugh and a death rattle. He thinks it’s possible that his soul just died a little.

Even Velazquez says, “Uh, Greenberg…” and then trails off like he’s too embarrassed to actually point out the guy’s _really_ obvious mistake.

Danny’s a good-natured guy, though. Especially when he’s dealing with obvious charity cases. “Greenberg, if nothing but vaginal sex actually counts as sex, then no sex I am ever going have will count. How stupid are you, man?”

Greenberg starts to sputter something, and Stiles isn’t sure whether he can actually deal with hearing another word come out of the guy’s mouth, which is why he jumps in himself.

“Anal sex totally counts as sex,” Stiles says. “That’s why it’s called anal _sex_. And if your girlfriend’s been doing it unprotected that’s more reason to use a condom, dude, not less. STDs are not cereal box toys, you do _not_ want to collect them all.”

“Fucking right,” Danny says.

Stiles regrets that they aren’t standing closer, because he’s pretty sure that right now they could be sharing a manly fist-bump and bonding over their mutual appreciation for useful knowledge.

Greenberg mostly just looks uncertain, like he’s used to people just nodding along and not contradicting him. It makes sense, because he’s best friends with Velazquez, who has a tendency to nod even when nobody’s talking to him, just to cover his bases.

“It’s her idea, she’s the one who wants to do it. I’m not going to turn her down just because you guys are jerks, okay?”

“Hey, I’ve got nothing against anal,” Danny says. He turns back to his locker and starts pulling on his shirt, like he wants to be ready to hit the eject button on this conversation as soon as humanly possible. “Anal’s awesome. But wear a condom. No glove, no love. It’s pretty simple.”

“Or don’t,” Stiles offers. He shrugs like he doesn’t give a shit, because sometimes the best love is tough love. “When Coach benches you because you’ve caught gonorrhea and your balls swell up like balloons, he’ll have to move me up to first line. So do what you want, I guess.”

Greenberg snaps, “Hey, screw you, Stilinski,” but Stiles’ ploy has clearly worked, because the kid’s frowning like that possible vision of the future is completely unacceptable. After a long pause, he says, “But even if I wanted to use a condom, it’s not like I can just buy them. My mom _owns_ the pharmacy. Plus everybody knows her. She’ll totally find out.”

That’s when Stiles remembers that he still has the paper bag in his backpack, the one that Ms. McCall pushed into his hands at the hospital. He says, “Dude, I’ve totally got you covered,” and he makes a victorious noise when he unearths the package from his pack. It’s kind of squished, and actually it looks less now like a brown-bag lunch and more like he deals marijuana from his locker. The contents aren’t worse for wear, though; Stiles tests a few of them, squeezes the packets between his fingers and finds that there’s still air in there, the packages haven’t been punctured.

He presses a couple condoms into Greenberg’s hand, looks the kid in the eye and says, “We never speak of this.”

Greenberg looks about as wide-eyed as he probably would’ve been if Stiles _had_ been carting around a brick of weed.

Danny, on the other hand… Danny’s just staring like he’s never even _seen_ Stiles before.

Which is how Stiles knows that it’s Danny’s fault when Miranda Heeney corners him after second period the next day — in the _boys’ bathroom_ — and says, “Stiles, hey. I heard you have condoms.”

After that, things kind of snowball. (No, not that kind of snowball, although Stiles does know about that because when he researches things he’s _thorough._ ) Stiles becomes basically the most popular kid in the entire school overnight, but it’s not like it gives him any actual social status. The opposite happens, actually. People start ambushing him every time he thinks he’s alone, and he’s not sure if he can actually develop PTSD from something like that, but between the student body and his personal history with creatures of the night, he starts to feel like somebody’s _always_ lying in wait for him.

A startlingly large percentage of the student body suddenly wants face time with him, which should be good, but in practice he actually becomes even more of a social pariah. Everybody knows he’s the kid with the condoms — and dental dams and single-use packets of lube, as it turns out — but nobody wants to _admit_ to knowing that. Which means nobody wants to admit to knowing _him_. Nobody wants to be seen so much as talking to him, except for the handful of really irritating douchebags who make a point to try to engage him in exaggerated winks and high-fives at lunch, to try to give everybody else the impression that they’re actually having lots of sex. They aren’t. Stiles doesn’t waste condoms on them anymore, because condoms are precious resources and they’re for actual dicks, not figurative ones.

Scott thinks it’s hilarious, which is why Stiles has decided that they’re not best friends anymore. He’s informs Scott of this at lunch, after Ian and Nathan have done their normal drive-by, throwing him thumbs-up and shouting, “Stilinski! My man!” Scott’s laughing with his face bowed down over his plate like his applesauce is doing something hilarious, and it’s seriously the last straw.

“I’m firing you as my best friend,” Stiles tells him. “I’m downgrading you to beta-friend. Maybe even omega-friend. I’m going to find a new alpha-friend. Consider yourself replaced.”

Scott doesn’t seem worried. He waggles his eyebrows and says, “Wow, Stiles, I didn’t know you thought about Derek that way. Is alpha-friends like friends with benefits, or…? I mean, you’re the sex expert, I don’t want to get all up in your area here.”

“I sincerely hate you.” Stiles chews morosely on his crappy cafeteria fries. “Do you have any idea the kinds of questions I’m fielding all day? It’s obvious to me now in living Technicolor detail that the Beacon County education system is falling down on the job when it comes to sexual education. I mean, obviously, they’re letting Finstock teach it, but it’s worse than I thought. A girl this morning tried to ask me about periods. What do I know about periods?”

Scott snorts. “Probably everything, once you get in some computer time.”

“You know me too well, Scott,” Stiles says. “Although, it is nice that all that research I did on male circumcision finally came in handy. Twice.”

“I don’t even want to know, dude. But, um, speaking of dicks—”

“Oh my _god,_ ” Stiles groans, and drops his head onto the table. “What even is my _life._ ”

“Come on, Stiles. You’re the guy with the condoms now, so…”

“So since when do you need condoms? I thought you and Allison weren’t supposed to be seeing each other. Something about her dad shoving a gun in your face? Actual mortal peril, is this ringing any bells?”

Scott just looks morose now, stirring his spoon through his applesauce with a sad face on. “I can’t _not_ see her. I’m in _love_ with her, Stiles, that doesn’t just go away.”

Stiles sighs. “You have like seriously _no_ self-preservation skills at all, you do know that.”

“Yeah,” Scott agrees. “But you’re going to help me anyway.”

“I’m totally going to help you anyway. I’m going to be optimistic on your behalf, man. I’m going to give you like a _lot_ of condoms later, for good luck, and in the name of all condom-carrying virgins everywhere. May you go in peace and have wonderful consenting sexual relations with the person or persons of your choosing.”

And if it means that Stiles can avoid ever having this kind of conversation with Allison, that’s just an added bonus.

4.

Stiles manages to avoid that conversation for all of three hours, until Allison goes the extra mile and actually shows up _at his house._ To ask him sex questions.

To be fair, she seems almost as embarrassed about it as he is. She twists her hands together all the way up the staircase and when she sits down on the edge of his bed it’s _right_ at the edge, like she wants to be prepared to fling herself out the window if things get too mortifying. Stiles knows the feeling, but he’s taken a seat in his desk chair, which places him closer to the window, which means _he_ gets first dibs on throwing himself out of it.

“So, Scott and I are probably going to have sex soon,” Allison says. It’s a hell of an opening, but Stiles has always liked that about her, how straightforward and unafraid she always seems. She’d be an open book, if it weren’t for the wide variety of secret horrors that is her life. “I mean, I want to have sex with him soon. We haven’t really talked about it.”

“I figured,” Stiles says. “I didn’t actually want to _know,_ for the record. But I figured. So what’s the problem? Don’t tell me you came for condoms, because I already loaded Scott up with a serious supply.”

“You did?” Allison narrows her eyes.

“I totally did. Which means you’re definitely on the same page there, so that’s a good thing, right? You guys talk about stuff, right? I don’t think asking is going to be a problem. There is no universe in which he says no.”

“Yeah, that’s not even remotely the problem. I just… um. I have a few concerns.”

“Okay,” Stiles says. It’s magnanimous of him, he thinks. He might be a little bit gay, but not actually for Scott. He doesn’t really want to picture Scott in any compromising positions, but he can’t always get what he wants. He’s willing to take one for the team, here, because if there are any two people on the face of the planet who do not need to complicate their already-complicated situation with something like an unexpected pregnancy, it’s these two. So Stiles is ready. He can handle this. He’ll be fine.

“Okay, so I was wondering what you know about, um… werewolves. And sex. Like werewolf sexual… practices.”

He’d like to say he’s surprised by this question, but he’s actually not. He isn’t exactly _prepared,_ though, because: “Nothing. I know absolutely one hundred percent of nothing about werewolves and sex. Isn’t that sad? I tried, Allison. I knew the day was coming when I would need to know, although I was _totally_ sure it was only going to come up because of like supernatural sex pollen scenario or actual heats or something and it was all going to come up at the worst possible time. But basically, if you ask Google about werewolf sex, all you get is a lot of really X-rated fiction and artistic renderings, and none of it really _seems_ like it’s been written by anybody who knows that werewolves exist, much less what their mating call sounds like.”

“Yeah, that’s about as far as I got with it, too,” Allison says. Her shoulders actually slump and she looks down at her lap like this dearth of information is the saddest thing that’s ever happened in her life. “And most of that fiction wasn’t even well-written, either.”

“Oh god, _tell_ me about it. But hey, do you think knotting is a real thing?”

Allison laughs. “I was going to ask _you_ that!”

“Hey, I’m not the one in this conversation who’s getting all personal with werewolf dicks, you tell me!”

“When he’s human, he’s _all_ human,” Allison says, with a shrug. “But I guess… I mean, I don’t know. Couldn’t that change if we were actually, you know, _mating_? Do you think they even call it that?”

“Probably, since it sort of sounds like something a weirdo sex offender would say.” Stiles drums his fingers against the underside of his chair, thinking hard. “Well, I mean, have you asked Scott? It _is_ his dick.”

Allison shrugs, looks away, which is a no. “I’m not sure he’d even know. It’s not like we’ve gone all the way before. And it’s not just that, it’s— I mean, what if he’s only in control until he isn’t? There’s so much about this whole werewolf thing that we don’t know. I borrowed a book out of my dad’s collection while he wasn’t looking… there was a whole chapter in there about a wolf who tore his human girlfriend apart in his ‘passion.’”

Stiles nods, seeing where she’s going with this. “So what’s the line between fiction and hunter propaganda. And also, what’s the deal with their dicks. That’s a pretty succinct line of questioning, I think. I can work with that.”

“Work with it? How? We have no resources. At all. And it’s not like I’m going to ask my _dad._ That won’t exactly end well.”

“Well, I don’t think he’d want me to call him a _resource,_ ” Stiles says. “I don’t think he’d want me to call him, period. And he is a master of crypticness. But Derek should know these things. I mean, The Talk’s got to go a little different when you’re a supernatural creature, right?”

Allison’s eyes go wide. Stiles likes to think that she’s just awed by his bravery, but— “You _can’t_ ask Derek Hale. He will actually kill you. Possibly with his bare hands. Like he did to his own uncle _literally_ just days ago.”

“Yeah, exactly,” Stiles says. “ _Literally_ just days ago we saved that guy’s life, practically killed the Alpha _for_ him, and let ourselves in for a lifetime of psychological scarring and horrible nightmares. He screwed Scott out of possibly becoming human again. He _owes_ us. The _least_ he can do is answer a few embarrassingly personal questions. I’m calling him.”

“You can’t just _call_ him,” Allison says, sounding almost scandalized. “Does he even have a phone? Why do you have his _number_?”

“We’ve embarked on fact-finding missions together before,” Stiles says, trying to sound casual even though his thumb almost shakes when he holds it over Derek’s name on his contacts list. It doesn’t even say “Derek” on it, just “D,” which he’s going to have to change because he feels like he should make a _wants the D_ joke about _himself_ right now and that’s not acceptable. “We’re already study-buddies. We are friends in research. We are totally— Derek! Hey! It’s. Uh. Stiles.”

“I noticed,” Derek’s voice says in his ear. Derek sounds his usual level of pissed off, so that’s good. It’s nice to start from a good baseline. “What do you want?”

“I have some questions for you. Some important, vital questions.”

“About something that’s actively threatening your life right now?”

“Um. Yes?”

Derek hangs up on him.

When Stiles calls back, the phone rings for a stupidly long time and then dumps him into voicemail. He tries again and gets the same result.

“Oh, it is _on,_ ” Stiles says, staring at his phone like it, personally, has betrayed him. “You don’t know what I can do with an Internet autodialer, asshole. I will _ruin you._ ”

“Stiles, maybe it’s not—” Allison starts.

Then there’s a thump on the roof outside, and the window slides open. Stiles jerks back so hard that he falls out of his chair — that’s really not funny anymore, to anyone, least of all him — but at least this time he lands sort of on the bed, and Allison catches him before he can actually hit the floor.

Derek just stands there, kind of awkwardly, hands in his pockets, shoulders a little hunched, as if he’s come in the front door and he can’t figure out why they’re so surprised to see him. “You said you wanted something?” he finally prompts, when Stiles and Allison just stare at him with their mouths open. He glances uneasily at Allison, like he’s afraid this is some sort of trap or she’s there to steal his awesome werewolf secrets.

“And you… actually came,” Stiles says. He thinks he might be hallucinating. This can’t be real. Derek Hale is volunteering to surrender information. Stiles might faint.

“I owe you one,” Derek says, ducking his head like just the _idea_ of owing somebody pisses him off. “And I was only like a block away, anyway. So ask me your stupid questions.”

Stiles feels vindicated, because _yeah_ , Derek owes them like _a million,_ but he also feels offended, because, “ _Stupid_ questions? How do you know they’re stupid? I’ll have you know that we are incredibly intelligent individuals.”

“ _Stiles._ ” Derek grabs the desk chair with clawed hands, like he’s trying to get a point across — if the point is that he’s a dick, it definitely works — and pulls it over by the window, starts kicking his feet up on the edge of Stiles’ desk. “Just _ask_.”

“Okay,” Stiles says. “Sure. So, werewolf dicks.”

Allison coughs like her horror has gotten stuck in her throat. Derek’s just putting the heel of his second boot up on the desk and he misses completely, his foot dropping straight down through thin air, overbalancing him. The only reason _he_ doesn’t go flying out of his seat is werewolf reflexes, which is _so_ unfair.

Derek takes a second to collect himself, and then he emphatically puts his foot up where he’d meant to put it, tries to look completely disinterested, and says, “What about them, specifically?”

It turns out knotting isn’t actually a thing, and Stiles won’t even admit to being _slightly_ disappointed about that. Derek doesn’t even know what they’re talking about, at first, and Stiles has to show him an Internet video of two dogs fucking. It’s possibly a low point in Stiles’ life, standing in front of his computer while the hottest guy he’s ever seen and the second-hottest girl he’s ever seen crowd around him to watch what probably constitutes weird bestiality porn.

“And they’re just stuck together like that? For _how_ long?” Derek looks completely horrified. “You think my dick does _that?_ ”

“Hey, I don’t think about your dick,” Stiles says, and oh, fuck, that was a blatant lie, that was an actual blatant lie and—

Yeah, Derek’s looking at him funny now because possibly his heart rate has just ramped up so hard and so fast he might actually die from it.

“You’ve never seen dogs mate before?” Allison says casually, dropping back onto the bed. She’s completely oblivious to the drama playing out before her very eyes. “It’s kind of hilarious. They just stand there for like half an hour when they’re done, looking like they’re stuck together at the ass.”

“You’re spending too much time with Scott,” Stiles tells her. “So the knotting thing’s out. Thank god. Like what would you even _do_ while you were stuck to another person? Finish the crossword together?”

“If the rest of your questions are going to be this moronic, I’m leaving,” Derek says flatly. He’s still staring at Stiles. He’s unnerving. Maybe he _should_ leave. Maybe _Stiles_ should leave. The state. Except—

“Uh, well, they’re probably not as stupid, but I do have more,” Allison says. There’s almost a question mark at the end, and her face makes that adorable little wince that pretty much everybody in the world is powerless to resist.

Derek settles back into his chair again, but he doesn’t put his feet up this time, like he wants to be braced for a quick get-away. “Alright,” he says, and Allison asks everything she can think of, one steady-voiced question at a time.

Stiles is _not_ going to tell Scott how many of Allison’s questions are about pregnancy and kids, because they might be getting ready to have sex but he’s not going to be the one to push them toward _that_ before they’re ready. And he’s also not going to tell anybody how many of Derek’s answers are a simple “I don’t know,” or the way he winces a few times (okay, a lot) like he’s remembering something really unpleasant. Derek squirms in his seat a lot and it’s not just discomfort with giving two idiot teenagers an impromptu supernatural sex talk, it’s just discomfort in general. There are a few pretty normal things Allison asks about that prompt a look on Derek’s face like he can’t even figure out _why_ anybody would want that. Overall, his attitude is not one of overwhelming sex-positivity.

But Stiles isn’t going to say a word. If there’s one thing he’s learned from Coach, it’s that safe spaces are sacred.

5.

Things settle down after that, for a while. Well, they settle down for certain values of “settle down,” because now Stiles is dealing with a murderous lizard, a new weirdness on the Lydia front, Derek recruiting a bunch of kids, an increasingly psychotic Argent family, an even more enigmatic Deaton (Stiles didn’t even know that was _possible_ ), and an exponential increase in life-threatening situations in general.

Things definitely settle down for Stiles’ unofficial side business, on the other hand, but only because he takes action on that front. He can’t deal with this shit _and_ a rampaging kanima, and he’s completely _over_ being interrogated about sexual positions by a ton of people who don’t actually want to have sex with him. So he calls up one of the hotline numbers that Ms. McCall gave him and asks them to send him some brochures. They clearly understand what he’s _not_ saying, and they send him an entire _box._

Stiles goes back to Ms. McCall to ask for more condoms; she raises an eyebrow, but she gives them to him anyway. Lots of them, _way_ more than last time, in a _much_ bigger bag.

“I was chatting with Miles down in the lab yesterday,” Ms. McCall says. “Apparently the last month has seen a precipitous drop in positive STD test results among teenagers in the area. I wonder why.”

“Wow, that’s weird,” Stiles says, trying to stuff the huge bag into his backpack and backing away slowly as if from a wild animal. “Still, a month doesn’t make a trend, right? I’ll have to ask my Stats teacher about that. Bye!”

His next move is talking to Jenny and Mikhail, who’ve been tossing around the idea of starting up a Gay-Straight Alliance since freshman year, and who are the only actual activists he knows. He sits down opposite them at lunch one day and says, “Something must be done.”

They both raise single eyebrows in what honestly looks like a practiced maneuver.

“About what?” Jenny says.

“Finstock. The Situation,” Stiles answers. The capital S is audible. “You guys know about the condoms. Everybody knows about the condoms.”

“That you have a shit-ton of them for reasons we don’t actually want to know about?” Mikhail says. “Yeah, everybody does know that.”

“Exactly,” Stiles agrees. “I can’t spend the rest of my high school career as the condom guy. Not to mention I’m kind of busy with lacrosse and like… my other activities.” He’s purposefully cryptic so they won’t ask. He’s at least learning something from being around all these fucking secret-keepers.

Jenny narrows her eyes like she suspects a trap. “What are you suggesting?”

“Condom fairies,” Stiles says. “A network of condom distribution, sticking it to the man so everybody can _stick it_ wherever they want, disease-free.”

Jenny and Mikhail exchange a look, like they’re sharing some sort of mind-twin communication.

“I’ve already got a ton of supplies and literature, I just need a more effective means of distribution. One man cannot bear this burden alone, and I personally am feeling done bearing it at all. Are you in?”

They’re not just in, they’re perfectly happy with the idea of cutting him entirely _out_. Jenny stops by the house the next day to pick up the stuff and Stiles is finally, blissfully free of it. He’s looking forward to hopefully surviving the rest of his high school career long enough to enjoy the blessed peace of only being ambushed by fanged animal-people.

The two of them turn out to be astoundingly efficient. It only takes a week before most people stop talking to Stiles completely, which feels like nature righting itself to its former balance. The Cure also seem to become surprisingly popular overnight, which Stiles normally wouldn’t notice except the kid at the locker next to Scott’s is wearing a Cure t-shirt on a Friday, and when Stiles points at it and says, “Are you in love, dude?” the kid just looks at him like Stiles is weird, like Stiles is possibly trying to hit on him in a strange and roundabout way. After that Stiles starts noticing The Cure t-shirts everywhere, at least one or two of them every day, and he realizes it’s the undercover condom fairy _uniform_.

It’s kind of genius, really, but more importantly, Stiles has made his escape from his unintentional foray into sex education.

Which is why he’s not at _all_ expecting what happens with Erica.

He wouldn’t be expecting Erica anyway, just in the normal course of events, because they’ve mostly put the bodily harm part of their relationship behind them now (he hopes), but that doesn’t mean Erica actually _likes_ him. So when he comes home from school and finds her lounging in his bed, he doesn’t think it’s _that_ weird to pinch himself and make sure he’s not having some kind of incredibly intimidatingly sexy dream. She’s still dressed, but she’s pulled the sheets back, and Stiles is sure he’s right in thinking that that’s not normal visitor behavior.

“Relax,” Erica says. She props herself up on her elbows and stares at him down the barrel of her cleavage. “I just thought it’d be funny if you could tell Scott you’d gotten a girl into bed without him being able to hear a lie.”

“And that’s why you’re my favorite,” Stiles says. He drops his backpack just inside the door, kicks off his sneakers, and drops himself into the chair, kicking his socked feet up on the end of the bed. “What’s up, wolf-girl?”

Erica prods at his toes with her own; she’s not wearing any socks, her viciously high heels are tumbled together artfully on the floor at the foot of the bed, and her nails are painted purple. “I have some sex questions. Derek said to ask you.”

It feels like approximately ten years before Stiles is able to snap his jaw shut, but it’s probably only five seconds, tops. “ _That’s_ why he actually answered our questions? So he could pawn off the awkward sex talks on somebody else?”

Erica shrugs. “Nobody ever gives him credit for what a clever asshole he can be,” she says, with a certain amount of pride in her voice.

“ _Preach,_ ” Stiles says, with feeling.

“But it’s not a bad idea. You’re really good at this stuff, I hear. Ellie Kropanin said you talked her through a pregnancy scare.”

“I convinced her to force her boyfriend to buy the test for her because he contributed to the problem. Since when do you hang out with Ellie Kropanin?”

“Girls’ bathroom.” Erica rolls her entire head back, like the really over-dramatic version of an eyeroll. “It’s a bustling hub of information you never actually wanted to hear.”

“Huh. The boys’ bathroom is mostly a collection of things you can’t unsee.”

“More like smells you can’t unsmell,” Erica says, wrinkling her nose. “I can’t even walk _by_ them anymore without my hand over my face. I don’t know how you deal.”

Stiles shrugs. “The lack of superpowers helps. So, what exactly did you want to know? Nothing about boys’ bathrooms, I’m willing to bet.”

“That’s not my major area of interest, no. I just… a lot of things have changed, since the bite. And I figured probably some of the sex stuff is different too, but it’s not like I’ve had sex before anyway, and then the Internet—”

“Betrays us horribly in this area, I know,” Stiles agrees, with a sigh. “So much kinky, kinky porno, and so little of it fact-checked.”

“I don’t think human porn is fact-checked, either,” Erica says. “I doubt pizza boys and plumbers really see that much action. But the werewolf stuff is definitely weirder. Like, knotting? Is that actually a thing?”

Stiles laughs just thinking about Derek’s face, watching those fucking dogs. “Not according to Derek,” he says. “Although he didn’t actually _show_ it to me, so he could just be protecting me from the truth.”

“You spend a lot of time thinking about Derek’s dick,” Erica says. It’s not a question. She’s also not wrong. “What if that just doesn’t happen if the guy’s, you know, still all human when he’s fucking? I’ve seen Derek’s Alpha form, it’s a lot more like a wolf. What if the knot only comes up when he’s in that shape and Derek just doesn’t know because he’s not kinky enough?”

“That’s a pretty decent theory,” Stiles says, because it is. He’s thought of it before. He’s thought of it fondly. He has occasionally thought about it at length, with his hand around his cock. “I didn’t think to ask.”

“You totally thought to ask, you just didn’t have the balls,” Erica retorts. She narrows his eyes at him, like she’s challenging his manhood, but since she’s always challenging his manhood he’s pretty accustomed to it. “Maybe I’ll ask him to _demonstrate._ ”

“Anything for science, huh?” Stiles says. He tries to narrow his eyes right back at her, but he’s pretty sure he mostly just looks squinty.

Erica huffs and looks away, like she can’t believe how stupid he is, which just proves that she doesn’t really know him all that well. She sighs dramatically (Derek must have taught her that) and sprawls back on his bed, stretching out, arching her back in a way that’s basically designed to play on his teenage hormones, and slides her hand across her belly. Her fingers ruck up her shirt, exposing the bare skin of her stomach, and Stiles can’t actually look away, even if he wanted to. Which he doesn’t. “If I got pregnant, do you think I’d have a baby, or a puppy?”

And that’s the exact moment when Stiles realizes that Derek didn’t send her at all, and she is absolutely, one hundred percent, just here to fuck with him. When she looks back at him the look on her face just confirms it. It is _on._

“Puppy, definitely,” he says. “Probably a Doberman. Has Derek ever mentioned to you that wolves mate for life? Like, if you meet your mate and he doesn’t love you back, you basically get to spend your whole life alone, pining. Also, I think there was something about physically feeling one another’s pain.”

“That doesn’t seem like a winning advantage, evolutionarily speaking,” Erica says. There’s a pleased little smirk on her face, like she’s happy that he’s chosen to engage. “Like if you’re taking on a bonded pair in a fight you only have to actually beat one of them? And then their poor puppies are left alone and defenseless.”

“What can I say? Your whole species doesn’t make sense. Like why would it be a _bite_ that turns a person into a werewolf? That just leaves your Alpha unable to use his frankly terrifying massive jaws to bite an enemy, because if they survive the attack they’re just going to be more powerful.” Stiles has issues with all of these things. It’s kind of nice to talk it out for once.

“I bet Derek’s a biter,” Erica says, contemplatively. She doesn’t seem to be talking about The Bite kind of biting, either. “My research indicates that might be a thing, too. Hickeys and things. Maybe I should let him know he’s free to _mark_ me anytime he wants.”

Stiles snorts. “How do you know ‘marking’ doesn’t mean pissing all over you? Maybe you’re into that, I’m not judging, I’m just saying since you _are_ sort of dog-people you really do have to be careful to define your boundaries.”

“ _Dog-people,_ huh? I guess I wouldn’t mind wearing a collar, under the right circumstances. Could be hot.” She looks up at him and puts on a fake sad-face, a pout that’s unfairly attractive considering how condescending it is. “I know you think about it, Stiles. I can smell it on you, every time you’re around him. I don’t blame you. I mean, we’ve got all that primal sex appeal, the toughness, the _endurance._ And Derek, he’s got all that _plus_ he’s the Alpha. I’ll bet his cock’s _huge._ I’ll bet he can keep it up all. Night. Long. What do you think he’s like, in bed? I bet he’s wild. He was _born_ an animal.” She rolls over, a little closer to the edge of the bed, stretched out on her front and propped up on her elbows. It gives him an unbelievable view of her cleavage that he isn’t even bothering to look at, because he’s actually considered this exact scenario in depth and mostly he can’t actually believe that she thinks all that. About _Derek._

Stiles says, “I—” and then he can’t figure out what exactly is supposed to follow that. His brain’s offline. Between the taunting and — he can admit it, he’s not too proud — the frequent mentions of Derek’s dick, he is unable to deal.

“Oh my God, Stilinski, seriously?” Erica says, when he continues to fail to produce any sort of actual sentence. “I can smell the hormonal stew you’re swimming in from here. And Derek _always_ stinks of sexual frustration these days, but mostly when _you’re_ around. I don’t want to hit you, but I _will._ ”

“Um,” Stiles says, because _what?_

“Ugh, you are the _actual worst,_ ” Erica says. She rolls out of the bed a lot less gracefully and seductively than she’s been for the rest of this adventure. She slips her feet back into her heels without even looking — that’s not a werewolf superpower, as far as Stiles knows, it’s just a girl superpower — and stalks angrily out the door, like she’s been personally wronged.

Stiles has _no idea_ what’s just happened.

+1

“So,” he says later, while he’s working his hands under Derek’s shirt. “Erica came by this afternoon.”

“I know.” Derek gasps the words against Stiles’ mouth. “She said you had labs or something. Homework.” His hands are already underneath Stiles’ clothes, his fingers tracing the line of skin at the waistband of Stiles’ jeans. “She came back smelling like she’d been rolling around in your bed.”

Stiles laughs and presses his open mouth against Derek’s throat, since it’s right there. “She _was_. Her reasoning was hilarious, but I see now that it was just a ploy to get you worked up. Also, we don’t have any labs together this semester.”

Derek actually pulls back a little at that, which is regrettable, but he’s still got Stiles pinned to the wall with his hips and his hands. The look on his face is worth it, anyway, because it’s equal parts pissed and impressed. “She _lied_ to me?”

“I know, she’s getting good, right? I bet you’d be proud, if only she’d chosen to use her powers for good rather than evil.”

Derek lets out a little laugh, leans in again just to press his nose against Stiles’ throat, which is a thing with him. “What did she actually want?”

“To yell at me until I made a move on you, I think,” Stiles says. “Apparently you reek of unfulfilled sexual desire. Do they seriously not realize that I made a move on you weeks ago?”

“They’re getting more observant, but they’re not quite there yet. Maybe we should give them some more obvious clues.”

Stiles is the one who pulls back this time — well, pushes back at least, because he’s kind of between a rock-like body and a hard wall — to make sure he’s reading this right. He has a well-earned reputation for saying things he really shouldn’t say, and he can’t actually afford to screw this up. “You’re going to have to spell it out for me, Derek. I’m totally happy with the make-outs, but if you want to try something else…”

“I want to try something else,” Derek says, looking him dead in the eyes, because they’ve had this talk already about being explicit with their needs and Derek has totally taken it to heart, at least where this is concerned. It’s _awesome._

Stiles smiles, slow and easy, fucking _happy,_ and leans in to taste Derek’s mouth again. He already knows the taste of it, the shape of it, knows what Derek’s body feels like beneath his and how the skin of Derek’s back is always hot and smooth. He never actually made out with anybody before Derek, never so much as _kissed_ anybody, but Derek’s _really_ good at it. Derek is a kissing connoisseur, and sometimes they just touch for hours, running their hands over each other. It makes Stiles feel like he’s going to catch fire, but it makes Derek almost drunk, like he’s starved for it and the sudden rush of sensation is enough to knock him off his feet. Even just the press of Stiles’ hand against the back of his neck makes his eyelids flutter shut and his breath gust out of his lungs.

They haven’t done anything else. Stiles has wanted to, sure, but the first time, _before_ that conversation about boundaries, things went a little too fast, and Stiles isn’t actually any good at this, but he’s trying, and it seems like it’s working between them. Stiles just _asks,_ now. Derek likes to hear him talk, anyway.

So he says, “What do you want to do?” His voice drops, deeper and softer, and he licks at Derek’s mouth so Derek can’t answer right away. This needs to be something Derek’s thought about, not just a spur of the moment offer.

Derek’s the one who draws the kiss deeper, reels Stiles in, and when he finally lets go they’re both panting. “I was thinking about your mouth,” Derek says. “Do you want to?”

“ _Fuck,_ yeah,” Stiles says, and when he surges away from the wall Derek just moves with him, lets himself be walked back toward the bed. It is absolutely one hundred percent sexy, the way Derek kicks off his shoes as he goes, the way his hands work at his own belt buckle, the way his eyes are fixed on Stiles’ face.

It’s also not actually a surprise to anybody when Stiles tries to do the same, manages to kick both his sneakers off but then _trips_ on one of them, grabs desperately for Derek and they _both_ go down. At least they hit the bed this time, instead of the floor. That doesn’t stop Derek from completely wolfing out, though.

It happens kind of automatically, on impact, like a deploying airbag; he hits the bed and his claws just pop out and his mouth is open with a long-toothed growl that even he seems surprised by.

“You are a fucking menace,” he says, but it’s a completely affectionate insult — Stiles is learning the difference.

“Whoa, wait, stay like that!” Stiles says, before Derek can change back.

Derek’s eyebrows go up — well, his _brows_ go up, he doesn’t actually have eyebrows anymore; Stiles is possessed by the sudden need to _find out where they went_ — and it turns out his sassy bitch-face is even more powerful when he’s slightly more canine. With the teeth and everything it just gives the impression that he sometimes plays with his food.

“Um, we had a theory,” Stiles says, which actually doesn’t help anything.

“We.” Derek’s voice is completely flat, not giving anything away, but he’s still sprawled across Stiles’ bed, which is kind of a great look for him. He props himself up on his elbows so he can direct his judging looks at Stiles more effectively, and that’s even _better_ somehow.

“Yes. Me. And, uh, Erica.” Stiles loses his train of thought because all of Derek is like _right there_ and he’s really good at lounging sexily and Stiles can see a little sliver of hip, where Derek’s shirt has ridden up, and it’s doing things to Stiles. Derek is _always_ doing things to Stiles, but for the most part those things have involved all their clothes being on, so they’re venturing into undiscovered country, here. “We had an idea. About knotting.”

“ _Stiles—_ ”

“Hear me out! It’s a totally good theory! What if there’s only a knot if you’re, you know, fooling around with your wolf face on? Have you ever?”

“You’ve seriously been discussing my dick with Erica.” Derek looks kind of put out, if that face can even be called that, but the important thing to note, which Stiles is _very much_ noting, is that Derek is still wolfed out. Like he’s staying that way. On purpose. _For Stiles._ Because Stiles wants him to.

“It’s _one question,_ for the sake of furthering our understanding of werewolf physiology.”

“It’s never _one question_ with you,” Derek says. He heaves out a put-upon sigh that makes his henley stretch over his chest in a really distracting way. “But no. I haven’t.”

“Not even just, you know… when you’re going solo?”

Derek huffs out a breath and turns his hands, still clawed, palms-up against the bed like, _See? Another fucking question mark. I called it._ But what he actually says is, “I’ve never been stupid enough to put my claws anywhere near my dick.” He flexes his fingers as if to demonstrate, and it’s very effective because yeah, Stiles wouldn’t risk it either.

“So you don’t know. You could have a knot and not even know. Wow, that was a tongue-twister.” Stiles puts his own hands against his thighs, and is acutely aware that he’s kneeling between Derek’s legs.

“So you’re saying you only want to see my dick for research purposes,” Derek says, and he’s teasing but there’s a bit of an edge to it, too, like he’s really not sure. He talks a little slower like this, enunciates more carefully around those seriously massive canine teeth. Stiles has never seen him like this at a time when nobody’s dying or about to be hideously maimed. It’s sort of weird but nice. Normal, almost.

“I feel like it’s important to be honest in these situations,” Stiles says. “All the literature talks about that. Building trust. Confiding in other people so they can confide in you. So I’m gonna say that’s a small part of why I want to see your dick, and the bigger part is because I have a lot of thoughts and feelings about you and your dick that have really nothing to do with werewolves or science or anything else. Mostly they have to do with me, and my dick, both of which have really fond feelings. About you. Also, we’ve been doing some seriously intense making out for like weeks now and you don’t even know how many times I’ve come in my pants lately, but you’re totally worth it. And if you decide you don’t actually want to show me your dick right now I’ll totally understand because um, I’m kind of weird and I think your werewolf face is sexy.”

Stiles can’t really read the look on Derek’s face, because his technique for interpreting Derek’s expressions is heavily reliant on eyebrows that are no longer there. But Derek says, “Come up here and kiss me,” so he does, lowering himself against the familiar heat of Derek’s chest, opening his mouth carefully against Derek’s, trying to keep their teeth from clattering together. It’s different and new with Derek’s excess of teeth, but it’s good, too, the same as it always is. Even if it’s a minor miracle that nobody ends up bleeding.

Then Derek grabs him by the jaw with one hand, and it’s unfathomably sexy, the span of his hand and the strength of his grip but also the delicate way he touches, with those claws out. Derek’s the one to readjust them, easing Stiles back a little, tilting both of their heads into better positions, bringing their mouths back together again. It’s easier this time, softer, sweeter, even with the teeth still there, sharp and deadly between them.

Stiles licks up the length of one of them, just because he can, and the sound that rumbles through Derek’s chest in response vibrates right through Stiles’ heart. Stiles doesn’t know whether it’s a warning or an encouragement, but he knows he likes it. A lot.

When Stiles finally has to pull back in order to breathe, Derek’s palms slide down his back, fingers held thoughtfully up and away so he won’t shred Stiles’ shirt. “You actually want to do this,” Derek says. “Like this.”

“I’d like to do it in any configurations and positions that turn you on,” Stiles answers. He sits up far enough to strip his shirt off, because if he’s going to have to stop to breathe he might as well multi-task. “Well, okay, not actually _any_. Like, I’m not all that flexible. And there’s stuff I don’t think I’m into. But we only do stuff we’re both comfortable with, so if you don’t want to do it like this… just, everything’s up for discussion, okay? We can talk about it. It’ll be good practice for you at using your words.”

“It’s your sparkling wit that I find the most attractive,” Derek says, but he doesn’t change back. He’s also sitting up and stripping his own shirt off, so he must not be all _that_ annoyed, and—

“Holy shit, _hair,_ ” Stiles says. “Okay, sorry, that was insensitive. But holy shit! You have chest hair! You’ve never had chest hair before. And I would know, I’ve seen you shirtless enough times to have memorized every detail.”

Derek huffs again — it’s his default non-word expression of disgust, dismay, and all the other things that Stiles regularly makes him feel — and drops back onto the bed.

“You shave. Your chest,” Stiles says. He feels like it needs to be said out loud. “When do you find the time to shave your chest? Does it always grow back when you wolf out? Wait, if you turn back right now will you have a shaved chest again?”

“Do you want me to?” Derek’s definitely looking annoyed now.

“No, it’s hot, I like it, I’m not judging your choices,” Stiles says. It is _really_ hot. He puts his hands down and pets it and it’s exactly as coarse as it looks. It’s not thick like the random sideburns that seem to just be a hilarious fact of werewolf life, it’s just natural, the kind of chest hair that any guy with Derek’s eyebrows (when he has eyebrows) might have. “You’re hot regardless of your personal grooming routine. Will you let me shave it, sometime?”

“You are the weirdest guy I have ever known,” Derek says. How it comes out sounding like a compliment is anybody’s guess, but it does.

“Yeah, but I’m also about to suck your cock,” Stiles replies, and ducks down to lick at Derek’s awesome chest hair.

“Jesus Christ,” Derek groans, and his hips flex upward almost unconsciously like just the thought of it is doing things for him, which is a _great_ start. “You’re going to have to take my jeans off, I can’t afford to buy more just because I’ve accidentally shredded them. Again.”

Stiles doesn’t need to be told twice; he scrambles back far enough that he’s got a little room to work with, kneeling again between Derek’s thighs, but he’s not going to rush this. He’s fantasized about this long enough that he feels perfectly justified in taking his sweet time.

He slips the top button slowly and inches down the zipper. Derek’s erection more or less unwraps itself, like the best present ever. It strains against the cloth, then bulges through the new opening until Derek groans and wriggles his hips and his cock pulls itself free. He’s staring at his own dick, staring at Stiles’ mouth, and his eyes aren’t dilated so much as they’re glowing really brightly, intensely red. It’s only like three parts freaky and seven parts unbelievably arousing.

“Right,” Stiles says. He gives Derek’s cock a thorough visual examination, then runs his fingers along the length of it. It’s longer than his own, but not quite as thick. It’s also really hard and it’s making Stiles think a lot of things that might not even be physically possible. “Well, it looks pretty normal so far, no knot in evidence. Also, I apparently have a thing for uncut penises. I hope you realize we’re on a journey of personal discovery here, Derek.”

“ _Stiles,_ ” Derek says, and Stiles has to seriously appreciate the way the guy can fit a whole paragraph into a single word. He sounds needy, exasperated, hungry.

Stiles is hungry, too. Stiles has needs. “I’m gonna go slow, okay?” he says, which maybe isn’t the most romantic ever.

“God, yes, just… fuck,” Derek says, so he probably wouldn’t appreciate eloquence on Stiles’ part anyway.

“Okay, hold on, I just need a con…dom.”

He realizes halfway through the word that there aren’t any condoms. There is possibly not a single condom _in his entire house._ Because for all that he’s been supplying them to the entire student population of Beacon Hills High for months, he never actually brought any up to his bedroom. They were just always around. They were extremely available and they sometimes taunted him with the thought of how much he didn’t actually need any of them and now he _does_ need one and he has _none._

“Oh my god, I don’t have any condoms,” he tells Derek, feeling like his entire world is caving in on him. “How can I not have any condoms?”

“Um?” Derek says, intelligently. He’s still watching Stiles’ mouth, like he’s enjoying seeing it move more than he’s listening to the actual sounds coming out of it. “I can’t really carry diseases,” he finally says. “With the healing, you know? There’s no risk.”

“Derek, Allison and I gave you a very general werewolf sex ed quiz and half your answers were _I don’t know._ So I hope you won’t be personally offended if I don’t feel like I can take your word for it. I mean, have you even _tried_ any Internet research on this subject? There are stories about _dudes_ getting pregnant, man. I’m not risking it.”

“I’m going to throw your computer out the window,” Derek says, and he actually sits up like he’s intending to do it right away, but then he digs gingerly into his back pocket.

“Really? A wallet condom? You realize heat and friction are not friends to latex, right? This is an actual crisis that you need to take seriously.”

What Derek actually pulls out of his pocket, though, is an Altoids tin. When he flips it open, a little clumsily because his fingers are still claws, it spills out a couple of condoms, a single-use lube packet, a lighter, and some packaged antiseptic wipes.

“Um,” Stiles says. “Okay, I can’t _not_ ask. What’s the lighter for?”

“It’s an emergency kit,” Derek says, looking down at the mess. “Most of my emergencies involve wolfsbane and gunshot wounds.”

“Oh,” Stiles says. He returns the lighter and the wipes to the tin, closes the lid gingerly and sets it on the bedside table. “So your emergencies are basically either the deadly kind or the sexy kind.”

“I don’t usually have the condoms. I’ve only been carrying them since we started. You know.”

Derek looks kind of bashful about it, but Stiles just grins, because that’s about as close as Derek gets to a declaration. They’re working on it.

The condom Stiles picks up isn’t anywhere near expired, and it’s also unlubricated, and Derek is seriously _the best._ Derek’s also still hard, which is great, because they are now officially ready to get this party started. Stiles climbs all the way off the bed, pulls Derek’s jeans the rest of the way off in a fashion that’s not really as smooth as it possibly could be, and then frantically pushes his own jeans and boxers down, taking care this time to _not_ do a faceplant because he’s pretty sure he’s reached his quota of unintentional physical comedy for the whole _month_ at this point.

The actual blowjob is a little awkward. Stiles is hunched over Derek’s dick and his back starts to twinge after a while, plus he can’t really go down very far at all without gagging. He has no idea how porn stars do it. Obviously practice is a factor, but maybe some people just have bigger mouths? He hopes Derek isn’t actually intending to throw his computer out any windows because he’s going to have shit to Google later.

He manages a good five minutes before he has to take a serious breather and try to lick the latex taste out of his own mouth. “Sorry, I know this isn’t very good,” he says, because he can be objective about his skills of head, and the fact is that he doesn’t have any. “I’ve never done this before.”

Derek says, “Me neither,” but the words come out breathy and panted so Stiles must be doing _something_ right.

“You’ve never gotten a blowjob?” Stiles says. He’s frowning because that idea is about the furthest thing from his perceived reality. Sure, Derek’s kind of abrasive and occasionally dickish, and Stiles has on occasion advocated for leaving him to die, but he’s also quietly funny, sarcastic, and hot like the sun.

“No, I’ve never given one,” Derek says, running a casual hand across Stiles’ scalp. He lets his claws drag a little on the way back, nape to brow, and it makes Stiles shudder, in a really good way. “Mine probably won’t be very good, either. But you’re doing fine. I like it. It’s… I like to look at you, your mouth on me.”

“Yeah?” Stiles says, and grins. He’s still holding Derek’s dick by the base, his hand slicked with his own saliva, his chin smeared with it, and he’s kind of a disgusting mess but it’s awesome, too.

“Yeah,” Derek agrees. “I want to try it, too. My mouth on you. I’ve been thinking about it both ways, about how it would be. It’s good, Stiles, it’s really good. I want it, I want _you,_ I want your mouth, please…”

Derek trails off, which is probably good because Stiles wouldn’t even be able to hear the rest through the rushing sound in his ears. Derek wants to keep having sex with him. _Derek_ wants to. With _him._ And maybe it’s obvious, or it should be, from the way Derek shaves more often now, keeps his jaw smooth so Stiles won’t complain about the stubble burn. Or the way he touches Stiles, like Stiles is something special to him, like skin against skin is all it takes to settle himself.

Stiles ducks his head and gets to work again with a new fervor, because he isn’t really known for mastering physical skills but he’s determined to acquire greatness in this one area, if nowhere else. He’s going to study Derek with all the intensity he’s been wasting on a thousand meaningless subjects. He’s going to research and meticulously catalog each of Derek’s reactions, to learn what makes him gasp, what makes him sigh, what makes him sink bonelessly against the bed.

When Derek comes, Stiles has taken him as deep as he’s able, and his hand is still stroking the base, his other palm doing its inadequate best to pin Derek’s hips to the mattress. Derek’s beautiful, the way he stretches against his own careful restraint, whimpering and flexing his hands and carefully not touching anything at all with those claws.

Stiles pulls himself off with an enthusiastic pop, gives himself a moment to ease his tired jaw, and then says, “That was _hot_. Totally glad we used that condom, though. I think I would’ve actually choked and that would have been really awkward for you to have to explain to my dad.”

Derek snorts, watching with hooded eyes and a satisfied expression as Stiles carefully eases the condom off, tying the end and crumpling a couple of tissues around it before he throws it in the garbage. By the time Stiles turns back, Derek’s back to human again (and his chest is _totally smooth again_ how does that even work) and his hands reach almost absently for Stiles’ body, stroking at his thighs, his shoulders, his chest. They haven’t even been naked together before, but Derek seems to like this re-drawing of their limits, just as skin-hungry as always.

Derek’s hand wraps around Stiles’ cock next, and Stiles isn’t even remotely too proud to admit that he grunts and pushes into it, wanting anything Derek’s offering.

Derek says, “We’ve still got another condom,” in a way that strongly suggests they put it to use.

Stiles grins, leans in for a less-toothy kiss, buries his fingers in Derek’s hair and then strokes them down his jaw, where those ridiculous sideburns used to be. “I don’t think one’s going to be enough. We’re going to need a supply.”

“Lucky for you I have no problem with just _buying_ them like a normal person,” Derek says, against Stiles’ mouth.

“Oh, thank god,” Stiles says, and reaches for the second condom, more than ready to continue with the hands-on portion of his ongoing research.

**Author's Note:**

> Yeeppppp that was 14K like wow that got out of hand quickly. SO, I have a few more endnotes but first I need to say that seriously, the Internet is an amazing tool for research on safer sex practices and you can use it for everything from learning a [condom song](http://www.youtube.com/watch?v=XR-xgZfXvTU) to learning how to [turn a condom into a dental dam](http://www.youtube.com/watch?v=RfouCcXDqJY).
> 
> I'd like to particularly recommend [Scarleteen](http://www.scarleteen.com/), which is geared toward teenagers but has excellent resources for people of all ages who would like to enjoy any sort of sexytimes. Their [questions and answers](http://www.scarleteen.com/article/advice) section is particularly fascinating reading.
> 
> Finstock’s line about his three rules to live by is lifted directly from the original _Teen Wolf_ movie. It’s my version of an homage, like how on the show they have Stiles wear ridiculous graphic t-shirts all the time. Also, Finstock gets all the best lines in every version of _Teen Wolf_. I kind of approve, except that I’m also scared of him.
> 
> The joke about doing a crossword while sexually tied is a reference to [State of the Union](http://archiveofourown.org/works/684099) by drunktuesdays. I highly recommend it, it is super-hilarious and also adorable. If you haven't read it yet I feel bad for you but I'm simultaneously envious because you still get to read it for the first time.
> 
> I found this promo while googling a random piece of Teen Wolf trivia for this fic. NEVER HAS A MORE APPROPRIATE VIDEO BEEN MADE. Check it out: [Teen Wolf: Sex Ed](http://www.youtube.com/watch?v=REy46CrHJNY)


End file.
